Diindeno[1,2-b:2′,1′-n]perylene: a closed shell related Chichibabin's hydrocarbon, the synthesis, molecular packing, electronic and charge transport properties† †Electronic supplementary information (ESI) available. CCDC 1050080–1050082. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc00652j Click here for additional data file. Click here for additional data file.

Kamal Sbargoud, Masashi Mamada,* Jérôme Marrot, Shizuo Tokito, Abderrahim Yassar* and Michel Frigoli* Diindeno[1,2-b:20,10-n]perylene, a new derivative of the indenoacene family was synthesized, and its electronic, electrochemical, and electrical properties were investigated. This material has a closed shell electronic configuration which corresponds to a quinoidal structure with a low band gap of 1.35 eV. Molecular packing in the single crystal was studied by single-crystal X-ray structural analysis, and this information was subsequently used in the determination of the charge transfer integrals via density functional theory methods. The charge-carrier transport properties of the diindeno[1,2-b:20,10-n]perylene-5,12-dione and diindeno[1,2-b:20,10-n]perylene derivatives were investigated through the fabrication and characterization of field-effect transistors via both vacuum-deposited and solutionprocessed films, respectively. Diindeno[1,2-b:20,10-n]perylene exhibited a field-effect behaviour with a hole mobility up to 1.7 10 3 cm V 1 s 1 when the active layer was solution-processed.